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Key West Road Trip: Funky Fun and Key Lime Pie

  • 19
  • 04:24
  • 188 mi
  • $20
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Created by Donna Hull - April 5th 2016

The stretch of Highway U.S. 1 that connects the Florida mainland to Key West is known for blue ocean views that reach to the horizon, world class fishing, fiery red sunsets, and water adventures both on top of and below the water. But this road trip is also wrapped in funky fun. Where else can you ride through the water on a famous movie set, have a tarpon jerk the bait from your hands as you kneel on a dock or watch fire eaters at sunset? And did I mention that key lime pie is available for breakfast, lunch and dinner? Let's hit the road for some funky Florida fun on the way to Key West. And, yes, we'll be tasting key lime pie at every opportunity.

Miami makes a good start for your Florida Keys road trip. Fly into Miami International Airport, rent a convertible and hit the road!

1
61mi 01h 13m
African Queen
4.5

Mile Marker 100, Key Largo, FL, US

African Queen

1

Would you like to cruise on a movie set? At Longboat Key, hop aboard the original vessel used in the filming of "The African Queen." When Captain Lance Holmquist stokes the steam engine, you'll chug a chug chug along a Key Largo canal on the 1.5-hour journey to the Atlantic Ocean and back. Or book a 2-hour dinner cruise that stops at Pilot House Restaurant for a 3-course meal. Yes, they serve Key Lime Pie for dinner.

2
18mi 00h 26m
Morada Bay Beach Café
3.9

Overseas Hwy, Islamorada, Village of Islands, FL, US

Morada Bay Beach Café

2

At Morada Bay Beach Cafe in Islamorada, outdoor dining comes with a blazing sunset. Sit at a colorful table on a sandy beach as slow jazz serenades from a loudspeaker. I recommend the coconut-crusted mahi mahi accompanied by coconut rice and broccolini, an excellent blend of Caribbean and American tastes. You'll want to order key lime pie for dessert, of course. If the scene looks eerily familiar, you're dining on one of the film sets of the Netflix drama series, "Bloodline."

3
0mi 00h 01m

82100 Overseas Highway, Islamorada, Village of Islands, FL, US

Islander Resort, A Guy Harvey Outpost

3

Islamorada deserves a couple of days for exploration (or more, if you have the time). Islander Resort, A Guy Harvey Outpost makes a fun headquarters. Accommodations include full kitchen, screened lanai, picnic tables and outdoor grills. You'll want to save time in your busy schedule for an afternoon or morning for lounging on the resort's sandy beach.

4
4mi 00h 08m
Robbie's Marina
5.0

77520 Overseas Hwy, Islamorada, Village of Islands, FL, US

Robbie's Marina

4

Want to feed a hungry tarpon? You can do it at Robbies Marina. Purchase a bucket of bait, then kneel on the dock as tarpon compete to yank the bait from your hand. Of course you'll also want to browse the eclectic mix of outdoor shops. When you're done shopping, stop in at the aptly names The Hungry Tarpon for a margarita, fish tacos and, you guessed it, key lime pie.

5
6mi 00h 09m
Whale Harbor Charters & Marina
3.4

83413 Overseas Hwy, Islamorada, Village of Islands, FL, US

Whale Harbor Charters & Marina

5

You can't come to the Florida Keys without offshore fishing. Head on over to Whale Harbor Charter & Marina in Islamorada. Spend the afternoon with Capt. Skip Bradeen on the Blue Chip Too where the fishing comes with stories of Capt Skip's 50 years of fishing in the Florida Keys.

6
3mi 00h 05m
Lazy Days Restaurant
4.4

79867 Overseas Hwy, Islamorada, Village of Islands, FL, US

Lazy Days Restaurant

6

Did you catch any fish with Capt. Skip? Head on over to Lazy Days Restaurant where the chef will cook up your catch. Did your line come up empty? That's okay, you can order from the menu. And there's key lime pie for dessert, too.

7
34mi 00h 45m
Seven Mile Bridge
4.3

Marathon, FL, US

Seven Mile Bridge

7

After a couple of days hanging out in Islamorada, it's time to continue this Florida Keys road trip. In Marathon, stop to walk the Seven Mile Bridge, listed on the National Register of Historic Places. Originally a railroad line constructed by Henry Flagler, the right of way eventually became a bridge on the Overseas Highway. At one time, Seven Mile Bridge was the longest bridge in the world. No longer drivable, cyclists and pedestrians are the only traffic. It's a great spot for photography, too.

8
16mi 00h 24m
Big Pine Kayak Adventures Inc.
5.0

1791 Bogie Drive, Big Pine Key, FL, US

Big Pine Kayak Adventures Inc.

8

There's still time for a water adventure before arriving in Key West. Why not stop at Big Pine Key for a kayaking adventure? You don't have to be an expert to explore here. Meet Bill Keogh of Big Pine Kayak Adventures at Old Wooden Bridge Fishing Camp for a 3-hour paddle through the mangroves at No Name Key. After the the adventure's over, look for the endangered key deer that live on Big Pine Key.

9
28mi 00h 42m
Hogfish Bar & Grill
4.5

6810 Front St, Stock Island, FL, US

Hogfish Bar & Grill

9

After walking the Seven Mile Bridge and kayaking at Big Pine Key, you're bound to be hungry. That's why you're stopping at Hogfish Bar & Grill on Stock Island for lunch. Order up a hogfish sandwich (a delicate fish caught by divers). Finish off lunch with a slice of key lime pie.

10
2mi 00h 08m

3824 N Roosevelt Blvd, Key West, FL, US

The Gates Hotel Key West

10

If you appreciate hip, sophisticated lodging that's a bit removed from the noise and hustle-bustle, The Gates Hotel Key West will hit your sweet spot. From the welcome rum drink to the sleek furnishings to an awesome pool, The Gates Hotel makes a fun choice. And it's on one of the trolley stops so you can leave the car in the parking lot when exploring the historic sights of Key West.

11
4mi 00h 11m
Mallory Square
4.5

1 Whitehead St, Key West, FL, US

Mallory Square

11

Set your watch to arrive at Key West's Mallory Square about two hours before sunset. You'll be treated to a quirky experience complete with street performers, arts and crafts booths, food trucks, and plenty of other tourists. A hush comes over the crowd when the blazing sunset makes an appearance. Bet you can't resist from oohing and ahhing as the fiery red ball dips behind Sunset Key.

12
0mi 00h 00m
El Meson de Pepe
4.0

410 Wall St Mallory Square, Key West, FL, US

El Meson de Pepe

12

After the Mallory Square fun, a short walk takes you to an authentic Cuban dinner at El Meson de Pepe. I recommend the Ropa Vieja, “traditional Cuban shredded beef stewed with fresh tomatoes, green peppers, onions and red wine.” And no day in Key West should ever end without a slice of Key Lime Pie.

13
0mi 00h 03m
Blue Heaven
4.6

729 Thomas St, Key West, FL, US

Blue Heaven

13

After a restful night at the Gates Hotel, let's go for a breakfast that will take you to heaven on Thomas Street, Blue Heaven, that is. You'll probably encounter a line, but the Lobster Benedict is worth it. And so is the Key Lime pie.

14
0mi 00h 02m
Old Town Trolley Tours
4.3

122 Simonton St, Key West, FL, US

Old Town Trolley Tours

14
15
0mi 00h 02m
Ernest Hemingway Home and Museum
4.5

907 Whitehead St., Key West, FL, US

Ernest Hemingway Home and Museum

15
16
0mi 00h 01m
Key West Butterfly Conservatory
4.6

1316 Duval St, Key West, FL, US

Key West Butterfly Conservatory

16
1mi 00h 04m
Half Shell Raw Bar
4.0

231 Margaret St, Key West, FL, US

Half Shell Raw Bar

Schooner Wharf Bar
4.0

202 William St, Key West, FL, US

Schooner Wharf Bar

Donna Hull

I'm a boomer traveler exploring the world one road at a time. I write about it at My Itchy Travel Feet, The Baby Boomer's Guide to Travel.